DE2234399A1 - SKIN PROTECTION PRODUCTS - Google Patents

SKIN PROTECTION PRODUCTS

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Publication number
DE2234399A1
DE2234399A1 DE2234399A DE2234399A DE2234399A1 DE 2234399 A1 DE2234399 A1 DE 2234399A1 DE 2234399 A DE2234399 A DE 2234399A DE 2234399 A DE2234399 A DE 2234399A DE 2234399 A1 DE2234399 A1 DE 2234399A1
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Germany
Prior art keywords
glycine
melting point
ester
acetyl
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
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DE2234399A
Other languages
German (de)
Inventor
Rolf Stefan Dr Brickl
Hans Dipl Chem Dr Eberhardt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Priority to DE2234399A priority Critical patent/DE2234399A1/en
Priority to ES416337A priority patent/ES416337A1/en
Priority to AT608773A priority patent/AT338434B/en
Priority to JP48079223A priority patent/JPS4985244A/ja
Priority to BE133542A priority patent/BE802414A/en
Priority to NL7309851A priority patent/NL7309851A/xx
Priority to AU58129/73A priority patent/AU483797B2/en
Priority to HUTO000918 priority patent/HU167186B/hu
Priority to DK392873A priority patent/DK133537C/en
Priority to GB3369973A priority patent/GB1436614A/en
Priority to CH1034873A priority patent/CH600873A5/en
Priority to CA176,467A priority patent/CA1022849A/en
Priority to DD172459A priority patent/DD107591A5/xx
Priority to FR7326126A priority patent/FR2192795B1/fr
Publication of DE2234399A1 publication Critical patent/DE2234399A1/en
Priority to US05/596,852 priority patent/US4016287A/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
    • A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/008—Preparations for oily skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Description

Hautschutzmittel In der Literatur werden zahlreiche Acyl-amino-carbonsäure-derivate (siehe beispielsweise C. A. 66, 29058 (1967)) beschrieben, in diesen Literaturstellen werden keinerlei biologische Wirkungsangaben gemacht. Skin protection agents There are numerous acylamino-carboxylic acid derivatives in the literature (see, for example, C.A. 66, 29058 (1967)) in these references no biological activity information is given.

Es wurde nun überraschenderweise festgestellt, daß die Verbindungen der allgemeinen Formel I, in der R1 ein Wasserstoffatom, einen geradkettigen oder verzweigten Alkylrest mit 1 bis 24 Kohlenstoffatomen, eine Trifluormethylgruppe, einen gegebenenfalls durch eine Alkylgruppe, ein halogenatom oder Nitrogruppe substituierten Phenylrest oder einen Biphenylrest, R ein Wasserstoffatom oder einen niederen Alkylrest mit 1 bis 3 Kohlenstoffatomen, R3 ein Wasserstoffatom, einen gegebenenfalls durch eine Methylthiogruppe substituierten Alkylrest mit 1 bis 6 Kohlenstoffatomen oder einen Benzylrest, R4 ein Wasserstoffatom oder einen geradkettigen oder verzweigten Alkylrest mit 1 bis 24 Kohlenstoffatomen und n die Zahl 0,1 oder 2 bedeuten, wertvolle therapeutische und kosmetische Eigenschaften besitzen, insbesondere zur Behand-.lung und Pflege der Haut.It has now been found, surprisingly, that the compounds of general formula I, in which R1 is a hydrogen atom, a straight-chain or branched alkyl radical with 1 to 24 carbon atoms, a trifluoromethyl group, a phenyl radical or a biphenyl radical optionally substituted by an alkyl group, a halogen atom or nitro group, R a hydrogen atom or a lower alkyl radical with 1 to 3 carbon atoms, R3 a hydrogen atom, an alkyl radical optionally substituted by a methylthio group with 1 to 6 carbon atoms or a benzyl radical, R4 is a hydrogen atom or a straight-chain or branched alkyl radical with 1 to 24 carbon atoms and n is the number 0.1 or 2, have valuable therapeutic and cosmetic properties , especially for the treatment and care of the skin.

Die Verbindungen der allgemeinen Formel I lassen sich gegebenenfalls in Kombination mit anderen Wirksubstanzen, z.B. mit Vitaminen, Corticosteroiden, Steroiden, Antihistaminika,.Keratolytlka, Antibiotika oder Desinfizienzien, in die üblichen zur Anwendung auf der Haut geeigneten Zubereitungsformen wie Salben, Cremes, Aerosole, Puder, Tinktur, Gele, Pasten, Essenzen oder Lotios in einer Konzentration von 0,1 bis 20.%, vorzugsweise 0,25 bis 5 S, einarbeiten. Gegenstand der vorliegenden Anmeldung sind somit neue Hautschutzmittel bzw..Mittel zur Behandlung und Pflege der Haut.The compounds of the general formula I can optionally in combination with other active substances, e.g. with vitamins, corticosteroids, Steroids, antihistamines, .keratolytlka, antibiotics or disinfectants, in the usual preparation forms suitable for use on the skin such as ointments, creams, Aerosols, powders, tinctures, gels, pastes, essences or lotios in one concentration from 0.1 to 20%, preferably 0.25 to 5 S, incorporate. Subject of the present Registration are therefore new skin protection agents or agents for treatment and care of the skin.

Die Verbindungen der allgemeinen Formel I, welche zum größten Teil literaturbekannt sind, lassen sich durch folgendes Verfahren herstellen: Acylierung einer Verbindung der allgemeinen Formel II, in der R2 bis R4 und n wie eingangs definiert sind, mit einem reaktionsfShigen Derivat einer Säure der allgemeinen Formel III, R1 - COOH (III) in der R1 wie eingangs definiert ist.The compounds of the general formula I, most of which are known from the literature, can be prepared by the following process: acylation of a compound of the general formula II, in which R2 to R4 and n are as defined at the outset, with a reactive derivative of an acid of the general formula III, R1 - COOH (III) in which R1 is as defined at the outset.

Die Acylierung erfolgt vorzugsweise mit einem reaktionsfähigen Derivat einer Säure der allgemeinen Formel III, z.B. ihrem Anhydrid oder-Halogenid, zweckmäßigerweise in einem Lösungsmittel wie Wasser in Gegenwart einer Base wie Natriumhydroxid oder Pyridin bei Temperaturen zwischen 0 und 100°C.The acylation is preferably carried out with a reactive derivative an acid of the general formula III, e.g. its anhydride or halide, is expedient in a solvent such as water in the presence of a base such as sodium hydroxide or Pyridine at temperatures between 0 and 100 ° C.

Wie bereits eingangs erwähnt, weisen die Verbindungen der allgemeinen Formel I wertvolle therapeutische und kosmetische Eigenschaften für die Behandlung und.Pflege der Haut auf. Sie besitzen insbesondere eine talgdrüsenhemmende, antiphlogistische, antiproliferative, schuppenhemmende, kapillarstabilisierende, lokalanästetische, hautpflegende, hautschützende und hautfeachtigkeitssteigernde Wirkung, wobei sich die Verbindungen der allgemeinen Formel I, in denen R1 einen niederen Alkylrest, eine Phenyl- oder Biphenylylgruppe, R2 und R3 Wasserstoffatome, R4 ein Wasserstoffatom oder einen Alkylrest mit 14 bis 18 Kohlenstoffatomen und n die Zahl 0,1 oder 2 b.edeuten, als besonders wirksam erwiesen haben.As already mentioned at the beginning, the compounds have the general Formula I valuable therapeutic and cosmetic properties for treatment and. care of the skin. In particular, they have an anti-sebum, anti-inflammatory, antiproliferative, anti-dandruff, capillary stabilizing, local anesthetic, skin-caring, skin-protecting and skin-enhancing effect, whereby the compounds of general formula I in which R1 is a lower alkyl radical, a phenyl or biphenylyl group, R2 and R3 are hydrogen atoms, R4 is a hydrogen atom or an alkyl radical with 14 to 18 carbon atoms and n denotes the number 0.1 or 2 b., have proven particularly effective.

Die wertvollen therapeutischen und kosmetischen Eigenschaften der.The valuable therapeutic and cosmetic properties of the.

Verbindungen der allgemeinen Formel I können beispielsweise nach folgenden Methoden nachgewiesen werden: 1. Bestimmung der Beeinflussung der Hautfettung nach der Glasklötzchen-Methode (siehe Schaefer und Kuhn-Bussius, Durch. Klin.Compounds of the general formula I can, for example, according to the following Methods are proven: 1. Determination of the influence of the skin lipid after the glass block method (see Schaefer and Kuhn-Bussius, Durch. Klin.

exper. Derm. 238, 429-435 (1970)): Aufgerauhte Glasklötzchen werden auf die zu messenden Hautpartien aufgedrückt. Das vorhandene Hautfett-macht die Glasklötzchen durchsichtiger. Anschließend wird die Transmission im Photometer gemessen. Vor der Messung der Rückfettung der Haut wird das vorhandene Hautfett mit Plastikfolie abgenommen. exper. Derm. 238, 429-435 (1970)): Roughened glass blocks are pressed onto the areas of skin to be measured. The existing sebum makes them Glass blocks more transparent. The transmission is then measured in the photometer. Before measuring the lipid replenishment of the skin, the existing skin fat is covered with plastic wrap removed.

Die zu untersuchenden Substanzen wurden halbseitig auf der Stirn bei 5-10 Versuchspersonen mit 0,25 ml einer 5%igen alkoholischen Lösung der jeweiligen Substanz gegenüber Kontrollen (0,25 ml Alkohol) aufgetragen. Nach 1 1/2 Stunden erfolgte die Folienentfettung und nach weiteren 3 Stunden wurde die Rückfettung bestimmt. Die prozentuale Steigerung der Durchsichtigkeit der aUgedrückten Klötzchen ist proportional der vorhandenen Hautfettmenge: substanz mittlere Extinktionswerte Kontrolle Behandlung Differenz N-Acetyl-glycin-hexadecylester 66,0 75,5 9,5 N-Acetyl-alanin-hexadecylester 66,5 74,0 7,5 N-Benzoyl-glycin-hexadecylester 62,0 78,5 16,5 N-Acetyl-sarcosin-hexadecylester 77,5 86,5 9,0 N-Octanoyl-glycin 60,0 78,0 18,0 2. Bestimmung der antiphlogistischen Wirkung am Dinitrochlorbenzol-Ekzem (siehe A.I. Scott, Brit. J. Dermatol. 77, 586 (1965-)): Die zu untersuchenden Substanzen wurden auf die rasierten Flanken von je 10 mit Dinitrochlorbenzol sensibilisierten Meerschweinchen als 5%ige alkoholische Lösung gegenüber Kontrollen (Alkohol) aufgetragen. Die Behandlung erfolgte 1/2 Stunde vor Auslösung der allergischen Reaktion mit einer 1,0 o/ooigen Lösung von Dinitrochlorbenzol in Aceton. Die visuelle Ablesung der Ergebnisse erfolgte nach 22 Stunden. The substances to be examined were placed on one side of the forehead in 5-10 test persons with 0.25 ml of a 5% alcoholic solution of the respective Substance applied to controls (0.25 ml alcohol). After 1 1/2 hours the film was degreased and after another 3 hours it was the refatting determines. The percentage increase in transparency of the printed Klötzchen is proportional to the amount of sebum present: substance mean extinction values Control treatment difference N-acetyl-glycine-hexadecyl ester 66.0 75.5 9.5 N-acetyl-alanine-hexadecyl ester 66.5 74.0 7.5 N-Benzoyl-glycine-hexadecyl ester 62.0 78.5 16.5 N-Acetyl-sarcosine-hexadecyl ester 77.5 86.5 9.0 N-octanoyl-glycine 60.0 78.0 18.0 2. Determination of the anti-inflammatory Effect on dinitrochlorobenzene eczema (see A.I. Scott, Brit. J. Dermatol. 77, 586 (1965-)): The substances to be examined were placed on the shaved flanks of 10 guinea pigs sensitized with dinitrochlorobenzene as 5% alcohol Solution applied to controls (alcohol). The treatment took place for 1/2 hour before triggering the allergic reaction with a 1.0% solution of dinitrochlorobenzene in acetone. The results were read visually after 22 hours.

Beispiel A N-Acetyl-glycin-octadecylester 3,0g Glycinäthylester-hydrochlorid und 15,0 g Octadecanol werden auf 1000C erhitzt und bei dieser Temperatur 3 Stunden lang Salzsäuregas eingeleitet. Nach dem Abkühlen wird die erstarrte Schmelze in 500 ml Ather aufgeschlemmt und der feste Rückstand des Glycinoctadecylester-hydrochlorids abgesaugt. Das rohe Ester-hydrochlorid wird in Wasser aufgeschlemmt und die Base unter Rühren durch Zugabe von Natriumbikarbonat im Überschuß freigesetzt, abgesaugt und getrocknet. Der Esterwird in 50 ml Acetanhydrid gegeben und eine Stunde auf dem Wasserbad erhitzt. Anschließend wird die Lösung in 1 l Wasser gegeben und die entstandene Fällung des acetylierten Esters abgesaugt und getrocknet. Zur Reinigung wird das Rohprodukt 3-mal aus Petroläther umkristallisiert.Example A N-acetyl glycine octadecyl ester 3.0 g glycine ethyl ester hydrochloride and 15.0 g of octadecanol are heated to 1000C and at this temperature for 3 hours long hydrochloric acid gas introduced. After cooling, the solidified melt is in 500 ml of ether and the solid residue of the glycine octadecyl ester hydrochloride sucked off. The crude ester hydrochloride is suspended in water and the base released with stirring by adding excess sodium bicarbonate, filtered off with suction and dried. The ester is added to 50 ml of acetic anhydride and left on for one hour heated in the water bath. Then the solution is poured into 1 liter of water and the The resulting precipitation of the acetylated ester is filtered off with suction and dried. For cleaning the crude product is recrystallized 3 times from petroleum ether.

Ausbeute: 2,1 g (26 % der Theorie), Schmelzpunkt: 78-79 C Beispiel B N-Octadecanoyl-glycin 7,5 g (0,1 Mol) Glycin werden in einer Lösung von 4,0 g (0,1 Mol) Natriumhydroxid in 150 ml Wasser gelöst. Dazu gibt man 30 g (0,1 Mol) Octadecanoylchlorid und schüttelt kräftig bs das Produkt-fest wird. Man säuert mit konzentrierter Salzsäure an, saugt ab und wäscht mit- Wasser nach. Nach dem Trocknen des Festproduktes wird es 2-mal aus Essigester umkristallXsiert.Yield: 2.1 g (26% of theory), melting point: 78-79 ° C. Example B N-octadecanoyl-glycine 7.5 g (0.1 mol) of glycine are in a solution of 4.0 g (0.1 mol) sodium hydroxide dissolved in 150 ml of water. Add 30 g (0.1 mol) Octadecanoyl chloride and shake vigorously until the product becomes solid. You acidify with concentrated hydrochloric acid, sucks off and washed with water. After drying of the solid product, it is recrystallized twice from ethyl acetate.

Ausbeute: 25 g (73 % der Theorie), Schmelzpunkt: 1200C Analog den Beispielen A und B wurden folgende Verbindungen hergestellt: (Siehe beispielsweise Rec. trav. chim. 77, 267 (1958) oder J. Am. Chem. Soc. 78, 172 (1956).Yield: 25 g (73% of theory), melting point: 1200 ° C. Analogously to the Examples A and B made the following compounds: (See for example Rec. Trav. chim. 77, 267 (1958) or J. Am. Chem. Soc. 78: 172 (1956).

N-Acetyl-leucin-hexadecylester Schmelzpunkt: 37 - 38°C N-Acetyl-methionin-hexadecylester Schmelzpunkt: 59 - 600C N-Acetyl-phenylalanin-hexadecylester Schmelzpunkt: 75 - 760C N-Acetyl-sarcosin-hexadecylester Schmelzpunkt: 58 - 590C N-Formyl-glycin-hexadecylester Schmelzpunkt: 64 - 6500, N-Propionyl-glycin-hexadecylester Schmelzpunkt/ 67 - 68°C N-Trifluoracetyl-glycin-hexadecylester Schmelzpunkt: 68 - 700C N-Benzoyl-glycin-hexadecylester Schmelzpunkt: 59 - 600C N-4-Phenylbenzoyl-glycin-hexadecylester Schmelzpunkt: 103°C N-4-Chlorbenzoyl-glycin-hexadecylester Schmelzpunkt: 85 - 860C N-4-Nitrobenzoyl-glycin-hexadecylester Schmelzpunkt: 102 - 10300 N-Acetyl-B-alanin-hexadecylester Schmelzpunkt: 65 - 660C N-Benzoyl-glycin-docosylester Schmelzpunkt: 78 - 790c N-Acetyl-glycin-dodecylester Schmelzpunkt: 59 - 600.0 N-Acetyl-glycin-tridecylester Schmelzpunkt: 65 - 660C N-Acetyl-glycin-tetradecylester Schmelzpunkt: 69 - 700C N-Acetyl-glycin-pentadecylester Schmelzpunkt: 73 - 740C N-Acetyl-glycin-hexadecylester Schmelzpunkt.: 74 - 750C N-Acetyl-glycin-heptadecylester Schmelzpunkt: 76 - 770C N-Acetyl-glycin-octadecylester Schmelzpunkt: 78 - 790r N-Acetyl-glycin-nonadecylester Schmelzpunkt: 79 - 800C N-Acetyl-glycin-eicosylester Schmelzpunkt: 83 - 840C N-Acetyl-glycin-docosylester Schmelzpunkt: 86 - 87°C N-Acetyl-alanin-hexadecylester Schmelzpunkt: 64 - 650G N-Acetyl-alanin-octadecylester Schmelzpunkt: 70 - 7100 - N-Acetyl-ß-alanin-eicosylester Schmelzpunkt: 760C N-Acetyl-ß-alanin-dodecylester Schmelzpunkt: 50 C N-Benzyl-ß-alanin-dodecylester Schmelzpunkt: 560C N-Acetyl-4-aminobuttersäure-tetradecylester Schmelzpunkt: 580C N-Acetyl-4-aminobattersäure-octadecylester Schmelzpunkt: 710 N-Benzoyl-4-aminobuttersäure-octadecylester Schmelzpunkt 760C N-Dodecanoyl-glycin Schmelzpunkt: 1200C N-Tetradecanoyl-glycin Schmelzpunkt: 12500 N-Hexadecanoyl-glycin Schmelzpunkt: 123-126°C N-Octadecanoyl-glycin Schmelzpunkt: 12000 N-Docosanoyl-glycin Schmelzpunkt: 12100 N-Octadecanoyl-alanin Schmelzpunkt: 1090C N-Dodecanoyl-valin Schmelzpunkt: 1070C N-Tetradecanoyl-valin Schmelzpunkt: 980C N-Octadecanoyl-valin Schmelzpunkt 9300 N-Dodecanoyl-leucin Schmelzpunkt: 109 C N-Tetradecanoyl-leucin Schmelzpunkt: 1020C N-Hexadecanoyl-leucin Schmelzpunkt: 88- 890C N-Octadecanoyl-leucin Schmelzpunkt: 960C N-Docosanoyl-leucin Schmelzpunkt: 98°C N-Hexadecanoyl-sarcosin Schmelzpunkt: 65-66°C N-Octanoyl-glycin Schmelzpunkt: 109°C N-Decanoyl-glycin Schmelzpunkt: 114°C N-Hexadecanoyl-ß-alanin Schmelzpunkt: 117-118°C N-Benzoyl-ß-alanin 0 Schmelzpunkt: 103-105 C N-4-Phenylbenzoyl-ß-alanin Schmelzpunkt: 103-105°C N-Dodecanoyl-4-amino-buttersäure Schmelzpunkt: 92-93 C N-Octadecanoyl-4-amino-buttersäure Schmelzpunkt: 100-102°C N-Benzoyl-4-amino-buttersäure Schmelzpunkt: 88-89°C N-4'-Phenylbenzoyl-4-amino-buttersäure Schmelzpunkt: 18100 N-Tetradecanoyl-sarcosin Schmelzpunkt: 51-52°C N-Octadecanoyl-sarcosin Schmelzpunkt: 71-72°C M-Dodecanoyl-alanin Schmelzpunkt: 104-105°C N-Dodecanoyl-phenylalanin Schmelzpunkt: 1000C N-Hexadecanoyl-phenylalanin Schmelzpunkt: 98-99°C N-Octadecanoyl-glycin-methylester Schmelzpunkt: 83-84°C N-Octadecanoyl-glycin-äthylester Schmelzpunkt: 82-83°C N-Octadecanoyl-alanin-methylester Schmelzpunkt: 76-77°C N-Octadecanoyl-phenylalanin-isopropylester Schmelzpunkt: 69-70 C Beispiel 1 Creme mit N-Acetyl-glycin-hexadecylester Zusammensetzung: N-@cetyl-glycin-hexadecylester 3,0 g Benzalkon A 0,1 g Cremophor 0 4,0 g Glyzerinmonostearat 4,0 g Lanette 0 5,0 g Walrat 3,0 g Cetiol V 10,0 g dest. Wasser ad 100,0 g Herstellung: Benzalkon-wird in 70° C warmem Wasser gelöst (I). In die Schmelze (7000) von Cremophor 0, Glyzerinmonostearat, Lanette 0, Walrat, Cetiol V wird die Wirksubstanz einsuspendiert (II). II wird in I bei 70°C einemulgiert, anschließend wird kaltgerührt.N-acetyl-leucine-hexadecyl ester Melting point: 37 - 38 ° C N-acetyl-methionine-hexadecyl ester Melting point: 59 - 600C N-acetyl-phenylalanine-hexadecyl ester Melting point: 75 - 760C N-acetyl-sarcosine-hexadecyl ester Melting point: 58-590C N-formyl-glycine-hexadecyl ester Melting point: 64-6500, N-propionyl-glycine-hexadecyl ester melting point / 67-68 ° C N-Trifluoroacetyl-glycine-hexadecyl ester Melting point: 68-700C N-Benzoyl-glycine-hexadecyl ester Melting point: 59-600C N-4-phenylbenzoyl-glycine-hexadecyl ester. Melting point: 103 ° C N-4-chlorobenzoyl-glycine-hexadecyl ester Melting point: 85-860C N-4-nitrobenzoyl-glycine-hexadecyl ester Melting point: 102-10300 N-acetyl-B-alanine hexadecyl ester. Melting point: 65-660C N-Benzoyl-glycine-docosyl ester Melting point: 78-790c N-acetyl glycine dodecyl ester Melting point: 59-600.0 N-acetyl-glycine-tridecyl ester. Melting point: 65-660C N-acetyl-glycine-tetradecyl ester Melting point: 69-700C. N-acetyl-glycine pentadecyl ester. Melting point: 73-740C N-Acetyl-glycine-hexadecyl ester Melting point .: 74-750C N-Acetyl-glycine-heptadecyl ester Melting point: 76-770C N-acetyl-glycine-octadecyl ester. Melting point: 78-790r N-acetyl-glycine-nonadecyl ester Melting point: 79-800C N-acetyl-glycine-eicosyl ester. Melting point: 83-840C N-acetyl-glycine-docosyl ester Melting point: 86-87 ° C N-acetyl-alanine-hexadecyl ester. Melting point: 64-650G N-acetyl-alanine-octadecyl ester Melting point: 70-7100 - N-acetyl-ß-alanine eicosyl ester melting point: 760C N-Acetyl-ß-alanine dodecyl ester Melting point: 50 C N-Benzyl-ß-alanine dodecyl ester Melting point: 560C. N-acetyl-4-aminobutyric acid tetradecyl ester. Melting point: 580C N-Acetyl-4-aminobutyric acid octadecyl ester Melting point: 710 N-Benzoyl-4-aminobutyric acid octadecyl ester Melting point: 760C N-dodecanoyl-glycine. Melting point: 1200C N-tetradecanoyl-glycine Melting point: 12500 N-hexadecanoyl-glycine. Melting point: 123-126 ° C N-octadecanoyl-glycine Melting point: 12,000 N-docosanoyl-glycine. Melting point: 12,100 N-octadecanoyl-alanine Melting point: 1090C N-dodecanoyl-valine Melting point: 1070C N-tetradecanoyl-valine Melting point: 980C N-octadecanoyl-valine melting point 9300 N-dodecanoyl-leucine melting point: 109 C N-tetradecanoyl-leucine melting point: 1020C N-hexadecanoyl-leucine melting point: 88- 890C N-octadecanoyl-leucine melting point: 960C N-docosanoyl-leucine melting point: 98 ° C N-hexadecanoyl-sarcosine melting point: 65-66 ° C N-octanoyl-glycine melting point: 109 ° C N-decanoyl-glycine melting point: 114 ° C N-hexadecanoyl-ß-alanine melting point: 117-118 ° C N-Benzoyl-ß-alanine 0 Melting point: 103-105 C N-4-phenylbenzoyl-ß-alanine Melting point: 103-105 ° C N-dodecanoyl-4-amino-butyric acid. Melting point: 92-93 C N-octadecanoyl-4-amino-butyric acid Melting point: 100-102 ° C N-benzoyl-4-aminobutyric acid. Melting point: 88-89 ° C N-4'-phenylbenzoyl-4-aminobutyric acid Melting point: 18100 N-tetradecanoyl-sarcosine Melting point: 51-52 ° C N-octadecanoyl-sarcosine Melting point: 71-72 ° C M-dodecanoyl-alanine. Melting point: 104-105 ° C N-dodecanoyl-phenylalanine Melting point: 1000C N-hexadecanoyl-phenylalanine melting point: 98-99 ° C N-octadecanoyl-glycine methyl ester Melting point: 83-84 ° C N-octadecanoyl glycine ethyl ester melting point: 82-83 ° C N-octadecanoyl-alanine methyl ester. Melting point: 76-77 ° C N-octadecanoyl-phenylalanine-isopropyl ester Melting point: 69-70 C Example 1 Cream with N-acetyl-glycine-hexadecyl ester Composition: N- @ cetyl-glycine-hexadecyl ester 3.0 g Benzalkon A 0.1 g Cremophor 0 4.0 g glycerol monostearate 4.0 g Lanette 0 5.0 g Walrat 3.0 g Cetiol V 10.0 g dist. Water to 100.0 g preparation: Benzalkon - is dissolved in 70 ° C warm water (I). Into the melt (7000) from Cremophor 0, Glycerinmonostearat, Lanette 0, Walrat, Cetiol V, the active substance is suspended (II). II is emulsified in I at 70 ° C., followed by cold stirring.

Beispiel 2 Creme mit N-Octadecanoyl-glycin Zusammensetzung: N-Octadecanoyl-glycin 1,0 g Benzalkon A 0,1 g Cremophor 0 4,0 g Glyzerinmonostearat 4,0 g Lanette O 5,0 g Walrat 3,0 g Cetiol V 10,0 g dest. Wasser ad 100,0 g Herstellung:-analog Beispiel 1.Example 2 Cream with N-Octadecanoyl-glycine Composition: N-Octadecanoyl-glycine 1.0 g Benzalkon A 0.1 g Cremophor 0 4.0 g glycerol monostearate 4.0 g Lanette O 5.0 g Walrat 3.0 g Cetiol V 10.0 g dist. Water ad 100.0 g Preparation: -analog example 1.

Beispiel 3 Salbe mit N-Benzoyl-glycin-hexadecylester Zusammensetzung: N-Benzoyl-glycin-bexadecylester 3,0 g Cremophor 0 6,0 g Cremophor A fest 1,0 g Wollfett 2,0 g Paraffinöl 45,0 g Vaseline ad 100,0 g Herstellung: Cremophor 0, Cremophor A fest, Wollfett, Paraffinol und Vaselin wird bei 70°C zusammengeschmolzen und die Wirksubstanz winauspendiert, anschließend wird Kaltgerührt.Example 3 Ointment with N-benzoyl-glycine-hexadecyl ester composition: N-Benzoyl-glycine-bexadecyl ester 3.0 g Cremophor 0 6.0 g Cremophor A solid 1.0 g wool fat 2.0 g paraffin oil 45.0 g Vaseline ad 100.0 g Manufacture: Cremophor 0, Cremophor A solid, wool fat, paraffin oil and vaseline is melted together at 70 ° C and the Active substance is suspended, then cold stirring.

Beispiel 4 Gel mit N-Acetyl-glycin-hexadecylester Zusammensetzung: N-Acetyl-glycin-hexadecylester 3,0 g Carbopol 940 0,6 g Triäthanolamin 0,6 g Cremophor EL 5,0 g Isopropanol 30,0 g dest. Wasser ad 100,0 g Herstellung: Die Lösung der Wirksubstanz, Cremophor EL und Triäthanolamin in Isopropanol wird-in die wässrige Lösung von Carbopol eingerilhrt.Example 4 Gel with N-acetyl-glycine-hexadecyl ester composition: N-acetyl-glycine-hexadecyl ester 3.0 g Carbopol 940 0.6 g triethanolamine 0.6 g Cremophor EL 5.0 g isopropanol 30.0 g dist. Water ad 100.0 g Preparation: The solution of the Active ingredient, Cremophor EL and triethanolamine in isopropanol is-in the aqueous Carbopol solution stirred in.

Beispiel 5 Badeessenz mit N-Acetyl-glycin-hexadecylester Zusammensetzung: N-Acetyl-glycin-hexadecylester 5,0 g Texapon N 25 30,0 g Comperlan OD 5,0 g Isopropanol 20,0 g äther. öl 2,0 g dest. Wasser ad 100,0 g Herstellung: Die Lösung der Wirksubstanz und des ätherischen Öls in .Isopropanol wird in die wässrige Lösung von Texapon N 25 und- Comperlan OD eingerührt.Example 5 Bath essence with N-acetyl-glycine-hexadecyl ester composition: N-acetyl-glycine-hexadecyl ester 5.0 g Texapon N 25 30.0 g Comperlan OD 5.0 g isopropanol 20.0 g essential oil 2.0 g dist. Water ad 100.0 g Preparation: The solution of the active substance and the essential oil in .Isopropanol is added to the aqueous solution of Texapon N 25 and Comperlan OD stirred in.

Iieispiei b Haartinktur mit N-Oetadecanoyl-glycin Zusammensetzung: N-Octadecanoyl-glycin 0,25 g Isoadipat 0,2 g Parfümöl 0,1 g Isopropanol 50,0 g dest. Wasser ad 100,0 g Herstellung: Die Wirksubstanz, Isodipat und Parfümöl wird in Isopropanol gelöst und anschließend unter Rühren Wasser zugegeben.Iieispiei b hair tincture with N-Oetadecanoyl-glycine Composition: N-octadecanoyl glycine 0.25 g isoadipate 0.2 g perfume oil 0.1 g isopropanol 50.0 g dist. Water ad 100.0 g Preparation: The active substance, isodipate and perfume oil is in isopropanol dissolved and then added water with stirring.

Beispiel 7 Trockenspray mit N-Acethl-glycin-hexadecylester Zusammensetzung: N-Acetyl-glycin-hexadecylester 3,0 g Span 85 o,4 g Frigen 11 A 3,0 g Frigen 12/114 40:60 93,6 g Herstellung: Die Wirksubstanz, Span 85 und Frigen 11 werden in einer Kugelmühle vermischt. Diese auf 1500 abgekühlte Mischung wird in die auf -40 bis -50°C abgekühlte Treibgasmischung langsam eingetragen und unter Rühren abgefüllt.Example 7 Dry spray with N-acethl-glycine-hexadecyl ester composition: N-acetyl-glycine-hexadecyl ester 3.0 g Span 85 o, 4 g Frigen 11 A 3.0 g Frigen 12/114 40:60 93.6 g Manufacture: The active ingredient, Span 85 and Frigen 11 are in one Ball mill mixed. This mixture, cooled to 1500, is poured into the -40 bis -50 ° C cooled propellant mixture slowly entered and filled with stirring.

Beispiel 8 Schaum-Aerosol mit N-Benzoyl-glycin-hexadecylester Zusammensetzung:: N-Benzoyl-glycin-hexadecylester 3,0 g Cremophor EL 1,O.g Tween 80 1,2 g Texapon N 25 0,8 g Athanol 94%ig 21,0 g Wasser dest. 57,0 g Frigen 12/114 60:40 16,0 g Herstellung: Die Wirksubstanz wird in Athanol gelöst (I). Cremophor EL, Tween 80 und Texapon N 25 wird in Wasser gelöst (II). I wird unter Rühren in 11 eingetragen und das erhaltene Konzentrat in Dosen abgefüllt. Nach dem Verschließen mit einem Ventil wird das Treibgas eingepreßt.Example 8 Foam aerosol with N-benzoyl-glycine-hexadecyl ester composition: N-Benzoyl-glycine-hexadecyl ester 3.0 g Cremophor EL 1, O.g Tween 80 1.2 g Texapon N 25 0.8 g of 94% ethanol 21.0 g of distilled water. 57.0 g Frigen 12/114 60:40 16.0 g Preparation: The active substance is dissolved in ethanol (I). Cremophor EL, Tween 80 and Texapon N 25 is dissolved in water (II). I is entered into 11 with stirring and the obtained Filled concentrate in cans. After closing with a valve, the propellant gas pressed in.

Beispiel 9 Creme mit N-Benzoyl-glycin-hexadecylester Zusammensetzung: N-Benzoyl-glycin-hexadecylester 3,0 g Benzalkon A 0,1 g Cremophor 0 4,0 g Glyzerinmonostearat 4,0 g Lanette 0 5,0 g Walrat 3,0 g Cetiol V 10,0 g Vitamin-A-Acetat 30 000, I.E.Example 9 Cream with N-benzoyl-glycine-hexadecyl ester composition: N-Benzoyl-glycine-hexadecyl ester 3.0 g Benzalkon A 0.1 g Cremophor 0 4.0 g glycerol monostearate 4.0 g Lanette 0 5.0 g Walrat 3.0 g Cetiol V 10.0 g Vitamin A acetate 30,000 I.U.

Vitamin E-Acetat 20 I.E.Vitamin E acetate 20 I.U.

dest.' Wasser ad 100,0 g Herstellung: analog Beispiel 1 Beispiel 10 Lotio mit N-Octadecanoyl-glycin Zusammensetzung: N-Octadecanoyl-glycin 3,0 g Span 40 3,0 g Cremophor 0 2,0 g Lanette 0 2,0 g Walrat 1,0 g Cetiol V 5,0 g Paraffinöl subl. 1 0 g Nipagin M 0,1 g dest. Wasser ad 100,0 g Herstellung: Span 40, Cremophor 0, Lanette 0, Walrat, Cetiol V und Paraffinöl wird bei 7000 geschmolzen und darin die Wirksubstanz gelöst. Dest.least. ' Water to 100.0 g Preparation: analogous to Example 1, Example 10 Lotio with N-Octadecanoyl-glycine Composition: N-Octadecanoyl-glycine 3.0 g chip 40 3.0 g Cremophor 0 2.0 g Lanette 0 2.0 g Walrat 1.0 g Cetiol V 5.0 g paraffin oil subl. 1 0 g Nipagin M 0.1 g dist. Water ad 100.0 g Production: Span 40, Cremophor 0, Lanette 0, Walrat, Cetiol V and Paraffin Oil is melted at 7000 and in it the active ingredient dissolved. Dest.

Wasser wird auf 80°C erhitzt und darin Nipagin gelöst, nach dem Abkühlen auf 700C wird die Fettschmelze eingetragen, homogenisiert und kaltgerührt.Water is heated to 80 ° C and nipagin dissolved in it after cooling The fat melt is introduced at 700C, homogenized and cold-stirred.

Beispiel 11 Shampoo mit N-Acetyl-glycin-hexadecylester Zusammensetzung: N-Acetyl-glycin-hexadecylester 3,'0'g Zetesol SE 35 T 55,0 g Tylose MH 300 4,0 g Nipagin M 0,5 g dest. Wasser ad 100,0 g Herstellung: Dest. Wasser wird auf 800C erhitzt, darin Nipagin M gelöst und Tylose suspendiert. In Zetesol und Parfümöl wird die Wirksubstanz mittels Schnellrührer verteilt,, dem Tyloseschleim zugegeben, homogenisiert und entlüftet.Example 11 Shampoo with N-acetyl-glycine-hexadecyl ester composition: N-acetyl-glycine-hexadecyl ester 3, '0'g Zetesol SE 35 T 55.0 g Tylose MH 300 4.0 g Nipagin M 0.5 g dist. Water to 100.0 g Production: Distilled water is heated to 800C heated, dissolved therein nipagin M and suspended gylose. In zetesol and perfume oil the active substance is distributed using a high-speed stirrer, added to the Tylose slime, homogenized and deaerated.

Beispiel .12 Puder mit N-Acetyl-glycin-hexadecylester Zusammensetzung: N-Acetyl-glycin-hexadecylester 3,0 g Aerosil 1,0 g Magnesiumstearat 0,2 g ANM Maisstärke ad 100,0 g Herstellung: In 1/3 der Maisstärke werden nacheinander Wirksubstanz, Aerosil und Magnesiumstearat gegeben und gut durchmischt. Anschließend wird die restliche Menge Maisstärke hinzugegeben und nochmals gut durchmischt.Example .12 powder with N-acetyl-glycine-hexadecyl ester composition: N-acetyl-glycine-hexadecyl ester 3.0 g Aerosil 1.0 g magnesium stearate 0.2 g ANM corn starch ad 100.0 g production: In 1/3 of the corn starch, active substance, Aerosil and magnesium stearate given and mixed well. Then the Add the remaining amount of cornstarch and mix well again.

Beispiel 13 Paste mit N-(4'-Phenylbenzogl)-4-aminobuttersäre Zusammensetzung: N-(4'-Phenylbenzoyl)-4-aminobuttersäure 3,0 g Lanogen 1500 20,0 g Isopropanol 45,0 g Veegum pharm. 10,0 g Pigment und Farbstoff 1,0 g Parfümöl 0,2 g dest. Wasser ad 100,0 g Herstellung: Die Wirksubstanz wird in Lanogen bei 6000 gelöst (I). Parfümöl wird in Isopropanol gelöst (II). Dest. Wasser wird auf 600C erwärmt, darin Veegum verteilt und quellen gelassen. Hierzu gibt man II und I, es wird durchgeknetet und homogenisiert.Example 13 Paste with N- (4'-Phenylbenzogl) -4-aminobutyric composition: N- (4'-phenylbenzoyl) -4-aminobutyric acid 3.0 g Lanogen 1500 20.0 g isopropanol 45.0 g Veegum pharm. 10.0 g pigment and dye 1.0 g perfume oil 0.2 g dist. Water ad 100.0 g Preparation: The active substance is dissolved in Lanogen at 6000 (I). Perfume oil is dissolved in isopropanol (II). Distilled water is heated to 600C, in it Veegum distributed and left to swell. For this you give II and I, it is kneaded and homogenized.

Beispiel 14 Tinktur mit N-Benzoyl-glycin-hexadecylester Zusammensetzung: N-Benzoyl-glycin-hexadecylester 3,0 g Isopropanol 25,0 g Xthanol 96%ig rein 25,0 g Parfümöl 0,2 g dest. Wasser ad 100,0 g herstellung: Isopropanol und Athanol werden auf 600C erwärmt und darin Parfümöl und die Wirksubstanz gelöst. Anschließend gibt man Wasser zu, kühlt ab und filtriert.Example 14 Tincture with N-benzoyl-glycine-hexadecyl ester composition: N-benzoyl-glycine-hexadecyl ester 3.0 g isopropanol 25.0 g xthanol 96% pure 25.0 g perfume oil 0.2 g dist. Water ad 100.0 g production: isopropanol and ethanol are heated to 60.degree. C. and perfume oil and the active substance are dissolved in it. Then water is added, the mixture is cooled and filtered.

Beispiel 15 Gel mit N-Acetyl-glycin-hexadecylester kombiniert mit einem Antibioticum Zusammensetzung: N-Acetyl-glycin-hexadecylester 3,0 g Chloramphenicol 0,1 g Salicylsäure 0,5 g Isopropanol 25,0 g, Bentone EW 2,0 g Triäthanolamin 1,8 g dest. Wasser ad 100,0 g Herstellung: analog Beispiel 15 Auf die gleiche Weise können alle Verbindungen der allgemeinen Formel I in die Ublichen Zubereitungsformen eingearbeitet werden.Example 15 Gel with N-acetyl-glycine-hexadecyl ester combined with an antibiotic Composition: N-acetyl-glycine-hexadecyl ester 3.0 g chloramphenicol 0.1 g salicylic acid 0.5 g isopropanol 25.0 g, Bentone EW 2.0 g triethanolamine 1.8 g least Water to 100.0 g Preparation: analogously to Example 15 In the same way all compounds of the general formula I can be used in the usual preparation forms be incorporated.

Beispiel 16 Gel mit N-Acetyl-glycin-hexadecylester kombiniert mit einem Antibioticum Zusammensetzung: N-Acetyl-glycin-hexadecylester 3,0 g Tetracyclin-HC1 0,1 g Salizylsäure 0,5 g Isopropanol 25,0 g Bentone EW 2,0 g Triäthanolamin 1,8 g dest. Wasser ad 100,0 g Herstellung: analog Beispiel 15 Auf die gleiche Weise können alle Verbindungen der allgemeinen Formel I in die üblichen Zubereitungsformen eingearbeitet werden.Example 16 Gel with N-acetyl-glycine-hexadecyl ester combined with an antibiotic Composition: N-acetyl-glycine-hexadecyl ester 3.0 g tetracycline-HC1 0.1 g salicylic acid 0.5 g isopropanol 25.0 g Bentone EW 2.0 g triethanolamine 1.8 g least Water to 100.0 g Preparation: analogously to Example 15 In the same way all compounds of the general formula I can be used in the usual preparation forms be incorporated.

Claims (7)

P a t e n t a n s p r ü c h eP a t e n t a n s p r ü c h e 1. Mittel zum schutze, zur Pflege und Behandlung der Haut, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung der allgemeinen Formel I, in der R1 ein Wasserstoffatom, einen geradkettigen oder verzweigten Alkylrest mit 1 bis 24-Kohlenstoffatomen, eine Trifluormethylgruppe, einen gegebenenfalls durch eine Alkylgruppe, ein Halogenatom oder Nitrogruppe substituierten Phenylrest oder einen Biphenylrest, R2 ein Wasserstoffatom oder einen niederen Alkylrest mit 1 bis 3 Kohlenstoffatomen, R3 ein Wasserstoffatom, einen-gegebenenfalls durch eine Methylthiogruppe substituierten Alkylrest mit 1 bis 6 Kohlenstoffatomen oder einen Benzylrest, R4 ein Wasserstoffatom oder einen geradkettigen oder verzweigten Alkylrest mit 1 bis 24 Kohlenstoffatomen und n die Zahl 0,1 oder 2 bedeuten.1. Means for protecting, caring for and treating the skin, characterized by a content of at least one compound of the general formula I, in which R1 is a hydrogen atom, a straight-chain or branched alkyl radical with 1 to 24 carbon atoms, a trifluoromethyl group, a phenyl radical or a biphenyl radical optionally substituted by an alkyl group, a halogen atom or nitro group, R2 is a hydrogen atom or a lower alkyl radical with 1 to 3 carbon atoms, R3 denotes a hydrogen atom, an alkyl group optionally substituted by a methylthio group with 1 to 6 carbon atoms or a benzyl group, R4 denotes a hydrogen atom or a straight-chain or branched alkyl group with 1 to 24 carbon atoms and n denotes the number 0.1 or 2. 2. Mittel zum Schutze, zur Pflege und Behandlung der Haut gemäß Anspruch 1, dadurch gekennzeichnet, daß mindestens eine Ver-Dindung in einen oder gegebenenfalls mehreren ueblichen Träger eingearbeitet wird.2. Means for protecting, caring for and treating the skin according to claim 1, characterized in that at least one connection in one or optionally several common carriers is incorporated. 3, Mittel zum Schutze, zur Pflege und Behandlung der Haut gemäß Anspruch 2, dadurch gekennzeichnet, daß als Träger Salben, Cremes, Aerosole, Puder, TinktureR,'aele, Pasten, Essenzen oder Lotios verwendet werden.3, means for protecting, caring for and treating the skin according to claim 2, characterized in that ointments, creams, aerosols, powders, tinctures, 'aele, Pastes, essences or lotios can be used. 4. Mittel zum Schutze, zur Pflege und Behandlung der Haut gemäß den AnsprUchen 1-3, dadurch gekennzeichnet, daß diese 0,1 -20 %, vorzugsweise Os25 - 5 %, an einer Verbindung der allgemeinen Formel I und gegebenenfalls weitere Wirkstoffe wie Vitamine, Corticosteroide, Antihistaminica, Steroide, Antibiotioa, Xeratolytica oder Desinfizienzien enthalten.4. Means for the protection, care and treatment of the skin according to the Claims 1-3, characterized in that this 0.1-20%, preferably Os25 - 5%, of a compound of the general formula I and optionally other active ingredients such as vitamins, corticosteroids, antihistamines, steroids, antibiotics, xeratolytics or disinfectants. 5. Verfahren zur Herstellung von Mitteln zum Schutze, zur Pflege und Behandlung der Haut, dadurch gekennzeichnet, daß mindestens eine Verbindung der allgemeinen Formel I in einen oder gegebenenfalls mehreren üblichen Trägerstoffen oder Verdflnnungsmittel eingearbeitet wird.5. Process for the preparation of means for protection, care and Treatment of the skin, characterized in that at least one compound of the general formula I in one or, if appropriate, several customary carriers or diluent is incorporated. 6 Verfahren zur Herstellung von Mitteln zum Schutze, zur Pflege und Behandlung der Haut gemäß Anspruch 5; dadurch gekennzeichnet, daß als Träger Salben, Cremes, Aerosole, Puder, Tinkturen, Gele, Pasten, Essenzen oder Lotios verwendet werden.6 Process for the preparation of means for protection, care and Treatment of the skin according to claim 5; characterized in that ointments are used as carriers, Creams, aerosols, powders, tinctures, gels, pastes, essences or lotios are used will. 7. Verfahren zur Herstellung von Mitteln zum Schutze, zur Pflege und Behandlung der Haut gemäß den Ansprüchen 5 und 6, dadurch gekennzeichnet, daß diese 0,1 - 20 %, vorzugsweise 0,25 - 5 %, an einer Verbindung der allgemeinen Formel I und gegebenenfalls weitere Wirkstoffe wie Vitamine, Corticosteroide, Antihistaminica, Steroide, Antibiotica, Keratolytica oder De8infizienzien enthalten.7. Process for the preparation of means for protection, care and Treatment of the skin according to claims 5 and 6, characterized in that this 0.1-20%, preferably 0.25-5%, of a compound of the general formula I and possibly other active ingredients such as vitamins, corticosteroids, antihistamines, Contain steroids, antibiotics, keratolytics or de-infectives.
DE2234399A 1972-07-17 1972-07-17 SKIN PROTECTION PRODUCTS Withdrawn DE2234399A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
DE2234399A DE2234399A1 (en) 1972-07-17 1972-07-17 SKIN PROTECTION PRODUCTS
ES416337A ES416337A1 (en) 1972-07-17 1973-06-27 Procedure for the preparation of new derivatives of acil-aminocarboxilic acids. (Machine-translation by Google Translate, not legally binding)
AT608773A AT338434B (en) 1972-07-17 1973-07-11 COSMETIC SKIN CARE PRODUCTS
JP48079223A JPS4985244A (en) 1972-07-17 1973-07-13
HUTO000918 HU167186B (en) 1972-07-17 1973-07-16
NL7309851A NL7309851A (en) 1972-07-17 1973-07-16
AU58129/73A AU483797B2 (en) 1972-07-17 1973-07-16 Dermatological compositions
BE133542A BE802414A (en) 1972-07-17 1973-07-16 SKIN PROTECTION PRODUCTS
DK392873A DK133537C (en) 1972-07-17 1973-07-16 MEDIUM FOR COSMETIC SKIN CARE
GB3369973A GB1436614A (en) 1972-07-17 1973-07-16 Dermatological compositions
CH1034873A CH600873A5 (en) 1972-07-17 1973-07-16 Acylaminocarboxylic acid compsns
CA176,467A CA1022849A (en) 1972-07-17 1973-07-16 Dermatological compositions comprising acylamino-carboxylic acid derivatives
DD172459A DD107591A5 (en) 1972-07-17 1973-07-16
FR7326126A FR2192795B1 (en) 1972-07-17 1973-07-17
US05/596,852 US4016287A (en) 1972-07-17 1975-07-17 Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof

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DE2234399A DE2234399A1 (en) 1972-07-17 1972-07-17 SKIN PROTECTION PRODUCTS
US37975173A 1973-07-16 1973-07-16
CH1034873A CH600873A5 (en) 1972-07-17 1973-07-16 Acylaminocarboxylic acid compsns
GB3369973A GB1436614A (en) 1972-07-17 1973-07-16 Dermatological compositions
FR7326126A FR2192795B1 (en) 1972-07-17 1973-07-17

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JP (1) JPS4985244A (en)
AT (1) AT338434B (en)
AU (1) AU483797B2 (en)
BE (1) BE802414A (en)
CA (1) CA1022849A (en)
CH (1) CH600873A5 (en)
DD (1) DD107591A5 (en)
DE (1) DE2234399A1 (en)
DK (1) DK133537C (en)
FR (1) FR2192795B1 (en)
GB (1) GB1436614A (en)
NL (1) NL7309851A (en)

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EP0011845A3 (en) * 1978-11-30 1981-05-06 Henkel Kommanditgesellschaft auf Aktien Antiseborrhoeic hair treatment composition
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US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
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US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
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US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds

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Publication number Publication date
AU5812973A (en) 1975-01-16
AU483797B2 (en) 1975-01-16
ATA608773A (en) 1976-05-15
CH600873A5 (en) 1978-06-30
BE802414A (en) 1974-01-16
NL7309851A (en) 1974-01-21
AT338434B (en) 1977-08-25
JPS4985244A (en) 1974-08-15
GB1436614A (en) 1976-05-19
DK133537B (en) 1976-06-08
DD107591A5 (en) 1974-08-12
FR2192795A1 (en) 1974-02-15
CA1022849A (en) 1977-12-20
FR2192795B1 (en) 1977-05-13
DK133537C (en) 1976-10-25

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